


Finding Boundaries

by SummerRoses0612



Series: Prompts/Pairings [25]
Category: Teen Wolf (TV)
Genre: Alternate Universe - Fraternity, Alternate Universe - Human, Anal, Anal Fingering, Anal Sex, Consensual Sex, DO NOT COPY, Frat Boy Danny Mahealani, Frat Boy Derek Hale, Frat Boy Ennis, Frat Boy Jackson Whittemore, Frat Boy Vernon Boyd, Fraternities & Sororities, Gay Sex, Implied Consent, M/M, Mildly Dubious Consent, Multi, Pledge Aiden, Pledge Ethan, Pledge Isaac Lahey, Pledge Stiles Stilinski, Rough Sex, Threesome, Threesome - M/M/M, do not copy to another site
Language: English
Status: In-Progress
Published: 2021-03-13
Updated: 2021-03-17
Packaged: 2021-03-22 06:27:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 2
Words: 3,410
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30034452
Author URL: https://archiveofourown.org/users/SummerRoses0612/pseuds/SummerRoses0612
Summary: When Stiles, Isaac, Ethan, and Aiden Pledge to be apart of ABO House, they are taken under the wings on some of the frat brothers.ORBasically an excuse for writing smutty sex between unusual pairings- as far as I can tell.
Relationships: Aiden/Ethan/Ennis (Teen Wolf), Derek Hale/Stiles Stilinski/Jackson Whittemore, Vernon Boyd/Isaac Lahey/Danny Mahealani
Series: Prompts/Pairings [25]
Series URL: https://archiveofourown.org/series/2182707
Kudos: 5





	1. Power Dynamics

**Author's Note:**

> This is a prompt from Ryan. Sorry for the wait.

With all of the research that Stiles had done beforehand, he knew that college wasn't going to be easy. His life had been extraordinarily boring- the only change from the mind-numbing high school classes achievements that didn't feel earned. Just some of the perils of coming from a broken home- he supposed. 

He and a couple of friends were all going to college together, The Twin Terrors and Scarf unwilling to let their Mischief cause chaos without being there to enjoy the aftermath. 

It only took a month for Stiles to realize that college was just high school for adults, which was when he had put on his scheming face and ignored the looks of excitement and dread his best friends/friends with benefits/roommates shared. 

-

"I have decided that we are joining a fraternity," 

Stiles said it unceremonially during dinner after an exhausting day, watching with a blank yet vaguely amused expression as Aiden and Ethan both spit out their water and Isaac choked on his pasta. 

The pale nineteen-year-old just sat back and watched them try and figure out their minds.

Isaac was the first to collect himself, distractedly thanking the twins for the smack on the back they had given him, "I hate your ideas. Every. Single. Time," His face was filled with genuine anticipation and a manic sort of joy that had made plenty of other people walk in the other direction. 

"Seconded," The twins said with raised hands, their twin speak and ability to mirror each other perfectly without any communication not failing them.

"Which one?" Ethan asked, leaning against his twin and watching them all with fond annoyance. 

He was the most responsible out of the group- the one that told Stiles and Isaac no when their mischief got to be too much and reminded Isaac and Aiden that there was more to life than just classes and parties. Not to say that he wasn't just as bad as the rest of them, his strategic schemes easily getting them into more trouble than all of the trio's other ones combined. He was organized disaster, like a missile with a target already picked when he comes up with a plan. 

"I've narrowed it down to ABO House, Deke, or Ox," He was pulling pamphlets out of literally nowhere, Isaac looking under the table and still not seeing where the hell they had come from. 

By the end of the week, any reservations any of them might have had were long gone, deciding to pledge themselves to ABO House and see where it went. 

-

Upon meeting the asshole head of house Stiles promptly decided that he wanted to sleep with him. Tall, dark, and mysterious was literally everything that Stiles always looked for in bed companions, another of the brothers- Jackson- also having caught his attention. He watched Ethan and Aiden watching Ennis and decided quickly that they were going to have him in their bed within the month if they were accepted. He watched Isaac clock onto Boyd and Danny with a startling amount of intensity. 

The entire house was on a stage, the brunette with pretty blue eyes that introduced himself as Jackson playing the crowd in a way Stiles had only ever seen one of his best friends do. Grumpy- Stiles knows his name is Derek but holy hell is he moody- was glaring silently from behind Jackson and watching the man with fondness that Stiles thought nobody else could probably see over the sheer heat of his scowl. The bulky African American Isaac was making moon eyes at had introduced himself as Boyd and the man next to him with dark, intelligent eyes stood next to him and said his name was Danny. Ennis looked to be the oldest of the bunch, probably one of the things that had him catching the twin's attention, his bald head and huge muscles warning people off even though Stiles could see the indulgent amusement in his eyes. 

Knowing his brothers/roommates/best friends/friends with benefits as well as he did, Stiles knew that they would be relentless until they got the men they had their eyes on in their beds. He was under absolutely no delusion that he wasn't the exact same. 

He took a couple of moments to feel genuinely sorry when he saw the predatory gaze his brothers were sporting before promptly joining them.

-

Grumpy and Jackass personally came to tell them that they had been accepted as Pledges, Jackson preening under Stiles' obvious observation while Derek just looked done with the world. 

His four best friends wolf-whistled sharply in the background all at the same time, suddenly extremely focused on the TV with innocent expressions when Derek whipped around to stare them down. 

_'This is going to be great'_ Stiles thought to himself as he watched the way the man's hips moved as they walked away.

"Stop objectifying tall, dark, and handsome," Aiden said teasingly from the other room when the door had just barely been closed, the chuckle they heard from Jackson telling them that they had definitely heard it.

"Why am I friends with you guys?" The brunette asked the room at large, ignoring their faux hurt expressions as he made the trek back to his room, "It such a shame Ennis, Boyd, and Danny couldn't be here as well," He told them with a disgusting, simpering smile- just as much of an asshole as his friends.

He laid in his room that night scheming how to get the objects of his affections to talk to him before deciding to play it by ear, knowing that his roommates were doing exactly the same thing. 

It was going to be a fun next couple of weeks...

* * *

_Sex stuff in the next chapters, just felt like I needed some backstory. Thanks for your patience, Ryan. (Roseriley0612@gmail.com) If you want to contact me for prompts/pairings or even just to talk about whatever email is there and comment section is always open. -Rose_


	2. Testing Boundaries

**Summary for the Chapter:**

> Derek/Stiles/Jackson

Stiles had pegged Jackson and Derek to be in some sort of relationship with benefits after his second time seeing him. It made him reevaluate for a moment before at the bar that night he saw Jackson making out with someone else while Derek watched.

_'That solves that moral dilemma_

He upped his efforts to seduce them; skimpy clothing, obvious flirting, and some light, borderline, stalking later he knew that he had their attention. 

-

Derek was walking out of his class when Jackson grabbed his arm and dragged him to the parking lot without a single word. The older man almost moaned when he saw what was happening, Jackass not even bothering to hide his hard-on. 

Stiles was a pair of booty shorts that was basically a speedo and shirtless. They were skin tight and black- hiding nothing as his abs and arms constricted. He was washing his car with his friends- the twins wearing matching pairs of some frankly indecent speedos, somehow managing to be less revealing than Stiles despite the fact that they were wearing less material. The curly-haired one was wearing a literal pair of booty shorts that were wet enough to cling to his body, the scarf around his neck completely out of place yet obviously the reason Stiles and the twins were laughing at him. 

"I know we gave you your nickname for a reason but-!" Aiden shouted from where he was focusing on cleaning the windshield before he was laughing again, Ethan on the other side cracking up as he cleaned the opposite side. 

"Please tell me it's multi-purpose," Stiles begged, his muscles clenched with laughter from he was leaning against the car.

"I used it as a cum rag once?" Isaac offered with a cheeky smirk, finally cracking up with the rest of them after a second of holding his composure. 

For all that Stiles pretended that he didn't realize Derek and Jackson were watching the pair knew that he knew because he had made eye contact while getting progressively more provocative. 

The four got their composure back before they finished cleaning that car, talking idly as Stiles twisted himself in several obscene positions to clean one thing or another. By the time that he was walking towards the pair with a towel on his shoulder, they just grabbed his hand and dragged him back to the House. The three that they were leaving behind wolf-whisted and Isaac spanked Ethan who moaned exaggeratedly, laughing again at the middle finger Stiles sent them without looking back. 

Derek took the lead when they got to his room, grabbing Jackson's hand and picking Stiles up with the other. The brunette groaned at the show of strength and leaned against Jackson for balance when the black-haired man kissed him within an inch of his life. 

"We're gonna have sex now, right?" Stiles asked for clarification once he was finally able to think again.

"Yup," Jackson said huskily from where he was lounging naked on the bed, watching the show.

The brunette and the blonde shared a look before looking at Derek simultaneously. 

"Yes," Derek consented easily, grinning wickedly at Stiles before throwing him next to Jackson on the bed.

Stiles hummed in pleasure when Jackson immediately got on top of him and took over where Derek had left off, kisses that promised so many things and wandering hands that said they were going to follow through. Stiles opened the nightstand drawer, looking for the lube, and just kissed Jackson in thanks when the man reached over him and grabbed the bottle from where it was buried in condoms. 

"I can bottom for you both?" Stiles suggested, slicking his fingers and pushing one into himself with a groan before any of them could respond. 

"Yes, please," Jackson moaned as he pulled the brunette in his lap.

Derek chuckled at the enthusiasm they were both showing before quickly stripping himself and laying down next to where Stiles was straddling Jackson. Stiles was rocking with the movements of his fingers, his erection brushing with Jackson's before the teen pulled back and put a condom on quickly. Stiles moaned in appreciation, having forgotten momentarily before he continued stretching himself open. He was up to three fingers before he realized that Derek was pinching his nipples.

"I'm not very sensitive there but my neck is. Hickeys are welcome- I love having marks," He explained easily, more focused on finding his prostate.

The black-haired man hummed thoughtfully before attacking Stiles' neck, the brunette already keening with the wet mouth on him and the thought of the bruises he would have later from how hard Jackson was holding his hips.

"I'm ready. Who's first?" The brunette said after a couple of minutes, removing his fingers and wiping them off on the sheets.

Derek and Jackson shared a look before they moved simultaneously, Jackson picking Stiles up from his lap and sitting him down on his chest as Derek became a line of heat against the brunette's back. Stiles was completely distracted as a wave of lust went through him but not enough to miss the telltale sound of lube being opened and feel Derek sheathing himself in a condom. 

"I am," Derek said, his lips so close to Stiles' neck that they brushed against him when he spoke.

Stiles shivered and groaned as he was forced open around Derek's cock. He was about average-sized if not slightly bigger but it was immediately clear he knew what to do with it, only taking a couple of minutes of grinding against his hold on Stiles' hips to find the brunette's prostate. Stiles threw his head back with a keen when the man behind him bit his neck roughly just the way he liked and pushed hard into his prostate at the same time. The brunette's entire body was shaking under the assault so much so that he almost forgot about Jackson. 

The blonde under him was watching with his intense, beautiful blue eyes. Derek was watching him back, the pair of them splitting their attention between each other and the way Stiles took Derek so prettily. 

"Do you want me to suck you off until you come or fuck you after Derek's done with you?" Jackson asked with a smile Stiles knew he could get lost in.

The brunette whined at the question, enjoying the groan against his neck Derek gave him when he compulsively tightened around the rod of flesh inside him. Between the bites on his neck, the cock abusing his prostate, and Jackson's smile Stiles was already on edge.

"I want you to fuck me after he comes inside me but I don't want to come yet," Stiles said between grunts and gasps.

He was straddling Jackson's large chest, a hand on it for balance and the other holding Derek's mouth onto his neck. Derek was holding onto his hips so tight that he knew he'd have bruises in the morning, forcing him back onto each of his punishing thrusts. Jackson had a hand on one of Stiles' thighs, his nails digging in hard enough that Stiles could already see the crescent-shaped marks he would be sporting for the coming weeks. His other hand had been teasing the underside of Stiles' cock but once Stiles said he didn't want to come yet he moved farther back, tracing Stiles' rim where he was stretched tight on Derek's cock.

The gentle touch on his burning rim had Stiles' ass fluttering around Derek, his chest heaving as he tried to remember to breathe through the overwhelming pleasure. 

Stiles' hands were holding onto Jackson's chest and Derek's neck like a lifeline. The brunette went back to resting his head on Derek's shoulder to expose more of his neck to the older man and in an effort to get more air. Stiles couldn't have told you how long it took but eventually the brutal pace he was being subjected to, at his great pleasure, changed. It was less controlled with a rough edge that made Stiles' toes curl. It only took a couple of minutes after that for Derek to come. 

The older man paused when he was almost completely withdrawn just to feel the way Stiles tightened around the head of his cock before shoving in as hard and far as he could and holding Stiles still on him. The hands around his hips got that much tighter and Derek's teeth tightened around the flesh of his neck as he came. Stiles just groaned at being forced to stay still but took the reprieve to try and get some of his breath back. His entire body was aching at the rough treatment in a way that only turned him on further, his cock an angry purple at the tip and leaking pre-come like a faucet. His cock and his ass ached for very different reasons but both made Stiles restless. He stayed as still as he could and focused on the way Derek was chewing on his neck through the aftershocks. 

When he was finally done Derek lightened his hold on Stiles and instead moved one up to his chest to help him rest against his own chest. His other hand went to Stiles' lower back, rubbing it soothingly as he pulled out gently. He hushed the brunette gently when Stiles cried out at being empty, licking soothingly over the huge bruise he could already see forming on Stiles where he had chewed on his neck. 

"Still want another round with Jackson?" Derek asked him as he soothed the teen resting on his chest. 

"Mhmm," Stiles said with heavy-lidded eyes after a moment of serious consideration. He made eye contact with Derek before turning to Jackson. "Where do you want me?"

The suggestive words made the blonde smirk. Jackson didn't say anything, just shared a look with Derek that had the man levering Stiles so that he was resting on the blonde's chest. Jackson took a moment to look at him, only giving Stiles enough time to barely catch his breath before he flipped them over. He didn't waste another second, moving so that he was pinning Stiles under him and letting the brunette hold onto Derek's hand and his shoulder for something to ground himself. He lined himself up with Stiles' raw entrance, only waiting for the teen to make eye contact and nod before burning himself inside his tight heat. 

Stiles' entire body tried to curl up when he was filled, the pain from his sore hole and pleasure at being full again making him want to hide until he was less overwhelmed but Jackson was between his legs and his arms were on opposite sides of his body. He whimpered pathetically, tucking his face into the nape of Jackson's back and holding on tight to Derek's hand while he wrapped his legs around Jackson's lower back and just held on.

"Good?" Jackson asked, adjusting himself to accommodate for the way Stiles wanted to be wrapped around him. 

"Mhhm," Stiles responded after a moment, brain slow from not coming and the overwhelming edge of it all. His cock had gone to half-mast when he was trying to get his breath back but he was completely hard against Jackson's abs again. 

Jackson had a hand under Stiles that helped the teen keep his head in Jackson's neck easier and took some of the pressure off his hips. His other hand was on Stiles' neck, using his thumb to keep Stiles looking up and to the left at Derek so that he could make some hickeys of his own along his prominent collar bones. He left the right side of the brunette's neck alone considering the fact that the bruises Derek had made there weren't for him. 

The blonde's hips started thrusting. His method was much different than Derek's was, all rolling pushes that made his cock hit every sensitive spot inside the brunette he hadn't even known he had. They weren't as rough as the black-haired man's but they were hard and directly on his prostate. The ball in his stomach hadn't loosened since Derek had fucked him but it was getting tighter and tighter the longer Jackson kept going. His body was shaking again with how much he wanted to come, nothing stopping him this time. 

Every time that Jackson hit his prostate directly his body clenched up, the tightening and releasing of his muscles making him sore like a really good workout did. He didn't move his face from where he was mauling Jackson's neck, keening and grunting in between wet, shallow breaths as he was fucked for a second time. 

Stiles came with a loud, long, desperate, whine- his entire body clenching tight enough to cramp up in some places and his hand holding onto Derek's like a lifeline. He was tight for several long minutes, Jackson shaking above him but never changing a thing about his pace whiles Stiles rode his orgasm out until he finally relaxed all at once. His hole fluttered around Jackson's cock through the aftershocks, his entire body shivering as his pleasure turned sharp and made him feel way more sensitive than usual. He leaned his head against the pillow, looking at Derek with tired eyes as his body shook and Jackson kept thrusting. 

Derek just kissed him gently and petted his head as Jackson fucked him. He was whining and whimpering with the overstimulation but never asked for Jackson to stop, letting the blonde use him until he forced himself inside a final time and came with a grunt smothered against Stiles' stretched neck. 

In the stillness that followed Jackson and Derek took turns kissing Stiles, the brunette pliant on the bed and more focussed on catching his breath than kissing. 

"Ten out of ten- would recommend," He muttered once he could think again, his voice hoarse from all his moaning. 

Derek and Jackson chuckled with him, the ladder carefully removing himself from Stiles' body before curling up behind him. Derek's heat enveloped him from the front, the pair cuddling him between them.

In the safety of their arms, Stiles fell asleep. Derek picked up his shirt off the floor and cleaned them both, hushing Stiles softly when the teen shifted in his sleep as Derek got the lube out of him, the pair finally following him to sleep after another couple of minutes.

* * *

_Hope you like it. Up next: Ennis, Ethan, and Aiden._


End file.
